Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Home in Winchester
Beautiful And Spacious Fully Renovated Farmhouse
Beautifully renovated 4 bedroom, 3 bathroom, spacious home.  Roku TV, fast internet, large yard where you can see the sunrise in the back of the home and the sunset in the front of the home.  Very close to the lake (less than 10 minute drive), close to many great nature spots, and University of the South, Downtown Winchester area, and the famous Jack Daniels Distillery.  8 people can be comfortably accommodated, and if extra sleeping arrangements are needed, we have a comfy couch!  W
21–28 FebProfessional Host,
£190 per night
4.84 out of 5 average rating, 117 reviews
Superhost
Cabin in Winchester
Private Dock - Best Cabin Tims Ford Lake
Great cabin located directly on Tims Ford Lake. Cabin has been updated and includes nice, well stocked kitchen as well as a deck (with grill). Enjoy our dock - fish, swim and use our two kayaks, paddle board and a canoe. Plenty of space to tie your boat up to our dock in a mostly private cove. Please read the guest access section for more details on lake access. Close to some great attractions - Jack Daniels Distillery (19 mi), Bonnaroo (25 mi), Univ. of the South (19 mi), Winchester (5 mi)
13–20 JanIndividual Host,
£325 per night
4.86 out of 5 average rating, 170 reviews
Guest favourite
Cabin in Estill Springs
Holliday Hide Away
1200 sq. ft. very rustic converted pole barn. The floors are stained concrete and the walls are rough saw mill hewn poplar boards. Located on 3 acres of beautiful well kept property. It does not border the lake but is surrounded by Tims Ford Lake and less than 5 minute drive to 3 boat docks and launches. Close to restaurants, shopping venues, hiking trails, water falls and golfing. Pool table, cornhole set, board games & cards in cabin. Visit historic Franklin County and surrounding areas.
24 Jun – 1 JulIndividual Host,
£95 per night
4.95 out of 5 average rating, 237 reviews

Popular amenities for Winchester holiday rentals

Stay near Winchester's top sights

Western Sirloin Steak House9 locals recommend
Holt's Diner6 locals recommend
SUNRISE (The Breakfast Place)16 locals recommend
Las Margaritas6 locals recommend
Kroger14 locals recommend
The Home Depot3 locals recommend

Other great holiday rentals in Winchester

Guest favourite
Home in Winchester
Deluxe 5BR Lakefront Home - 2 Docks & Boat Ramp
1–8 Nov
£883 per night
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Winchester
Luxurious New Build LakeHouse Tim’s Ford 4BR4Bath
22–29 Apr
£300 per night
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Winchester
Peaceful Lakehouse Perfect for a Getaway at TFL
25 Nov – 2 Dec
£222 per night
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Winchester
Beautiful Tim's Ford Lake House (Sleeps 20)
24 Apr – 1 May
£685 per night
4.97 out of 5 average rating, 74 reviews
Guest favourite
Cottage in Winchester
Tims Ford Lake! Modern Farmhouse
18–25 Oct
£159 per night
4.89 out of 5 average rating, 35 reviews
Guest favourite
Home in Winchester
Laketopia! Tims Ford Lake Resort with Golf Cart
12–19 AprIndividual Host,
£307 per night
5.0 out of 5 average rating, 37 reviews
Guest favourite
Cottage in Winchester
Gentleman Jack's Retreat- Lake Front on Tim's Ford
8–15 AugProfessional Host,
£376 per night
5.0 out of 5 average rating, 6 reviews
Guest favourite
Cabin in Winchester
The Cabins At Rivers Edge
7–14 MayIndividual Host,
£150 per night
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Winchester
Woodsy 6br Tim’s Ford Lake View Home, private dock
9–16 AugIndividual Host,
£715 per night
4.9 out of 5 average rating, 41 reviews
Guest favourite
Home in Winchester
Lovely Lake View Home at Twin Creeks Marina
13–20 Sept
£294 per night
4.93 out of 5 average rating, 99 reviews
Guest favourite
Home in Winchester
Roger Haven Retreat
26 May – 2 JunIndividual Host,
£147 per night
4.9 out of 5 average rating, 10 reviews
Guest favourite
Home in Winchester
Lakehouse
30 May – 6 Jun
£170 per night
5.0 out of 5 average rating, 26 reviews

Quick stats about holiday rentals in Winchester

Total rentals

120 properties

Rentals with a pool

40 properties have a pool

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

110 properties are a good fit for families

Total number of reviews

2.3K reviews

Nightly prices starting at

£8 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Tennessee
  4. Franklin County
  5. Winchester